The Exchanges

Q So the fundraising allowed you to ramp up excessive growth quickly. Was that, was that the key determinant for you then?

A Yeah, and to feel like we could place bigger bets and do more. So risk can take a lot of forms, and, like, obviously, investing involves risk, and VC involves extreme amounts of risk. Um, in our business, there's also creative risk. There's, like, doing, there's, there's trying to create and execute shows or creative ideas that haven't been done before, and that involves risks. And sometimes they fail, actually. Sometimes they fail, fail before they ever, ever even get out into the world. But the most successful Media properties are ones that are trying to do something that hasn't been done before. You know, Mystery Show, which is one of our shows, is a format that had not ever been done before in this medium. Um, you know, solving mysteries with a kind of personal point of view, but using real journalism to solve actual mysteries out in the world, and doing it in a way that feels like a film that had never been done before. That's one of our most successful shows. Startup, a reality show about starting a business, hadn't been done before in this medium. Reply All repeatedly does things on their show, it's shows about the internet, where they break format and come up with whole new formats for an episode, and it's when you do that that the audience really notices and you see growth, and so we wanted to be well capitalized to be able to take that kind of risk.

AI assessment note: “Yeah, and to feel like we could place bigger bets and do more.”

Q And were you nervous to leave the security of a, a, a, a financially secure consulting career for, for a potentially, uh, more risky, uh, podcasting startup in Gimlet?

A I was nervous, but, you know, when I met Alex pretty immediately, I recognized that he is a very special person, and he, um, like, I asked myself, is there a real market here, and is it big enough to spend the rest of my life doing, uh, doing work in, and do I have a partner who I really believe in, and I think, like, I could work with, um, for a very long time, and go through hard times with, and build something with, and the answer, um, To both of those things was yes. I mean, Alex is one of the best people in the world at what he does. He's one of the greatest editors, and he is a creative visionary, and I don't think you get that many opportunities in your life to, um, partner with someone like that.

AI assessment note: “I was nervous, but, you know, when I met Alex pretty immediately”

Q So the fundraising allowed you to ramp up excessive growth quickly. Was that, was that the key determinant for you then?

A Yeah, and to feel like we could place bigger bets and do more. So risk can take a lot of forms, and, like, obviously, investing involves risk, and VC involves extreme amounts of risk. Um, in our business, there's also creative risk. There's, like, doing, there's, there's trying to create and execute shows or creative ideas that haven't been done before, and that involves risks. And sometimes they fail, actually. Sometimes they fail, fail before they ever, ever even get out into the world. But the most successful Media properties are ones that are trying to do something that hasn't been done before. You know, Mystery Show, which is one of our shows, is a format that had not ever been done before in this medium. Um, you know, solving mysteries with a kind of personal point of view, but using real journalism to solve actual mysteries out in the world, and doing it in a way that feels like a film that had never been done before. That's one of our most successful shows. Startup, a reality show about starting a business, hadn't been done before in this medium. Reply All repeatedly does things on their show, it's shows about the internet, where they break format and come up with whole new formats for an episode, and it's when you do that that the audience really notices and you see growth, and so we wanted to be well capitalized to be able to take that kind of risk.

AI assessment note: “Yeah, and to feel like we could place bigger bets and do more.”

Q And, and from then it's been the meteoric rise of Gimlet. I mean, first quick question then, why did you not start a radio show or, you know, producing more seriously your own in 2009 when you had the insight that it was moving to digital?

A Well, I had, I did start radio shows. I had launched a show. The idea was to do almost like the daily show for public radio, so it was a nightly news and entertainment show. It had live music, comedy, and serious interviews, and what we found is to distribute it to a really large audience, there were actually a lot of gatekeepers that we had to go through, so we basically had to, market by market, we had to convince program directors at local radio stations all over the country to To pick up the show, to, to distribute it, and that meant that we actually weren't really working for the listener, we were working for this intermediary, and we found it hard to do something that was, like, actually ambitious and that carried creative risk in that scenario, and so, um, I sort of did, did do radio shows, but it felt to me like the really exciting thing, um, was happening in podcasting, like, there was just, there was more, um, Um, creative, ambitious, um, work happening there, and that was exciting in a new kind of way.

AI assessment note: “there were actually a lot of gatekeepers that we had to go through”

Q And were you nervous to leave the security of a, a, a, a financially secure consulting career for, for a potentially, uh, more risky, uh, podcasting startup in Gimlet?

A I was nervous, but, you know, when I met Alex pretty immediately, I recognized that he is a very special person, and he, um, like, I asked myself, is there a real market here, and is it big enough to spend the rest of my life doing, uh, doing work in, and do I have a partner who I really believe in, and I think, like, I could work with, um, for a very long time, and go through hard times with, and build something with, and the answer, um, To both of those things was yes. I mean, Alex is one of the best people in the world at what he does. He's one of the greatest editors, and he is a creative visionary, and I don't think you get that many opportunities in your life to, um, partner with someone like that.

AI assessment note: “I was nervous, but, you know, when I met Alex pretty immediately”

Q And you mentioned those three incredibly successful shows and incredible shows in themselves. Have Gimlet had any attempted, uh, shows that haven't worked out maybe? Has that ever happened?

A Yeah, we, we have a, um, we have a new show development team whose sole job is to create new shows, and we have a kind of methodology that we've developed around that that includes essentially prototyping, and so we will make an episode, we'll have an idea for a show, and we'll make an episode of it. We make it, we make enough of an episode to know, like, hey, is this gonna work? Like, how does this feel? Does it have the right elements? And we've certainly made episodes of show concepts that we felt like Either they weren't, what they weren't working, or it was going to take so much luck for it to work repeatedly, or it was working well enough, but it wasn't, it didn't feel exciting enough, and we didn't pursue them further.

AI assessment note: “we've certainly made episodes of show concepts that we felt like Either they weren't”

Q And, and from then it's been the meteoric rise of Gimlet. I mean, first quick question then, why did you not start a radio show or, you know, producing more seriously your own in 2009 when you had the insight that it was moving to digital?

A Well, I had, I did start radio shows. I had launched a show. The idea was to do almost like the daily show for public radio, so it was a nightly news and entertainment show. It had live music, comedy, and serious interviews, and what we found is to distribute it to a really large audience, there were actually a lot of gatekeepers that we had to go through, so we basically had to, market by market, we had to convince program directors at local radio stations all over the country to To pick up the show, to, to distribute it, and that meant that we actually weren't really working for the listener, we were working for this intermediary, and we found it hard to do something that was, like, actually ambitious and that carried creative risk in that scenario, and so, um, I sort of did, did do radio shows, but it felt to me like the really exciting thing, um, was happening in podcasting, like, there was just, there was more, um, Um, creative, ambitious, um, work happening there, and that was exciting in a new kind of way.

AI assessment note: “Well, I had, I did start radio shows. I had launched a show.”

Q And you mentioned those three incredibly successful shows and incredible shows in themselves. Have Gimlet had any attempted, uh, shows that haven't worked out maybe? Has that ever happened?

A Yeah, we, we have a, um, we have a new show development team whose sole job is to create new shows, and we have a kind of methodology that we've developed around that that includes essentially prototyping, and so we will make an episode, we'll have an idea for a show, and we'll make an episode of it. We make it, we make enough of an episode to know, like, hey, is this gonna work? Like, how does this feel? Does it have the right elements? And we've certainly made episodes of show concepts that we felt like Either they weren't, what they weren't working, or it was going to take so much luck for it to work repeatedly, or it was working well enough, but it wasn't, it didn't feel exciting enough, and we didn't pursue them further.

AI assessment note: “we've certainly made episodes of show concepts that we felt like... weren't working”

Q totally different company, and I'm quoting here, I'm quoting Alex, uh, and by different I mean worse. So how do you as the co-founder try and maintain this kind of sense of small company culture with deep links internally as you do grow excessively? I think you mentioned that you were going to be 65 or 70 staff. In two years time. How do you keep that small company culture?

A Yeah, we do it. So we do a few things to, um, to, uh, Gimla does have a culture. Um, I think it's a fairly strong culture, although we haven't been that explicitly about communicating it and what it is, and I think that's something we'll probably start to do. And the ways we, uh, I mean, I think the way culture gets communicated is the behavior of the leadership. And also you can design in certain kind of signs and language and vocabulary that people use. So we started something recently called Gimlet Guides, which is every new employee who starts at the company now. It's something we started just a few months ago. We didn't have at the beginning, but when we got to like 20 or 25 people, we decided to get formalized about the onboarding process into the company. And so now when you come into the company, you're introduced to someone who's called your Gimlet Guide. And Gimlet Guides are people who are selected because they Are, um, they get our culture, and they're very empathetic, and they have meant, like, they have it in them to be a mentor, and so it's sort of their job to also, like, establish and communicate what the culture is here, um, how we work, um, what we believe in, what we don't believe in.

AI assessment note: “we started something recently called Gimlet Guides”

Q now, and talking about Gimlet specifically, a question from a dear friend, Matt Hartman, who actually has just released his own podcast, uh, Doing Your Business, which is, is actually very brilliant, so a must check out to everyone there, but Matt asks, how do you decide which new shows to create? Is it about creating new shows for overlapping audiences, or do you try to expand to new demographics?

A Uh, Both. I mean, one way, so we certainly have, you know, the most recent show we launched is called Surprisingly Awesome, and we saw a segment in the market of people who are listening really because they want to learn something. They want to be entertained, but they want to learn something. Like, you're going on your commute, and you, if you can, um, spend 25 minutes listening to an episode about interest rates and learn more about how the economy works, that's really valuable. Mm-hmm. Mm-hmm. Mm-hmm. Mm-hmm. Do we have a host who listeners can connect to? Like, are they companionable? Do we want to hang out with them as listeners? And then three is narrative. Like, is there a story here? Is there, are we, do we have the, do we have the pacing and suspense and emotional payoffs to really hook people? Because those are the three things that when we see them are the ones, the shows that, that go biggest with, um, with large audiences.

AI assessment note: “Uh, Both. I mean, one way, so we certainly have”

Q and as a VC show now, uh, with your latest amazing episode, uh, The Pitch, I think it was called, being about your series A, we have to talk about The Rays. Mm-hmm. So in this show, you stated that constraint breeds creativity. So in your head, what were the dilemmas around raising the Series A, and what was the determinant that made you realise that raising it was right?

A Well, we'd had a pretty good first year. We had launched three or four shows, and all of them were doing well. Um, like, they had grown to, to scaled audiences, and they were doing interesting creative work, and unlike, I think, most sort of Silicon Valley startups that have started in the last year or two, we had revenue from the very beginning, because we were selling advertisements on our show. In fact, we had conversations with some VCs who we would begin to talk about revenue, and they're like, we don't want to hear it. Um, we're not actually interested in that. We want to see just a really steep user growth curve, and like, we know that if you get a large audience, you can worry about the revenue later. Um, but for us, actually, it was important to do it from the beginning, both because we wanted to prove out the business model, but also because we didn't want to, um, like, we actually felt like the advertising business model, the ads were part of the product, and that they It made sense to have them there from day one. And actually, the business was going so well that we thought we could have a way to self-fund our growth. We thought there might be a possibility if we continued to make these hits and churn them out at a pace, a certain pace, that we could actually use the cash flows to fund our growth, like the way normal businesses do. And That is actually a very exciti…

AI assessment note: “and so that was kind of our dilemma. Ultimately, we decided we had really ambitious plans”

Q now, and talking about Gimlet specifically, a question from a dear friend, Matt Hartman, who actually has just released his own podcast, uh, Doing Your Business, which is, is actually very brilliant, so a must check out to everyone there, but Matt asks, how do you decide which new shows to create? Is it about creating new shows for overlapping audiences, or do you try to expand to new demographics?

A Uh, Both. I mean, one way, so we certainly have, you know, the most recent show we launched is called Surprisingly Awesome, and we saw a segment in the market of people who are listening really because they want to learn something. They want to be entertained, but they want to learn something. Like, you're going on your commute, and you, if you can, um, spend 25 minutes listening to an episode about interest rates and learn more about how the economy works, that's really valuable. Mm-hmm. Mm-hmm. Mm-hmm. Mm-hmm. Do we have a host who listeners can connect to? Like, are they companionable? Do we want to hang out with them as listeners? And then three is narrative. Like, is there a story here? Is there, are we, do we have the, do we have the pacing and suspense and emotional payoffs to really hook people? Because those are the three things that when we see them are the ones, the shows that, that go biggest with, um, with large audiences.

AI assessment note: “Uh, Both. I mean, one way, so we certainly have”

Q and as a VC show now, uh, with your latest amazing episode, uh, The Pitch, I think it was called, being about your series A, we have to talk about The Rays. Mm-hmm. So in this show, you stated that constraint breeds creativity. So in your head, what were the dilemmas around raising the Series A, and what was the determinant that made you realise that raising it was right?

A Well, we'd had a pretty good first year. We had launched three or four shows, and all of them were doing well. Um, like, they had grown to, to scaled audiences, and they were doing interesting creative work, and unlike, I think, most sort of Silicon Valley startups that have started in the last year or two, we had revenue from the very beginning, because we were selling advertisements on our show. In fact, we had conversations with some VCs who we would begin to talk about revenue, and they're like, we don't want to hear it. Um, we're not actually interested in that. We want to see just a really steep user growth curve, and like, we know that if you get a large audience, you can worry about the revenue later. Um, but for us, actually, it was important to do it from the beginning, both because we wanted to prove out the business model, but also because we didn't want to, um, like, we actually felt like the advertising business model, the ads were part of the product, and that they It made sense to have them there from day one. And actually, the business was going so well that we thought we could have a way to self-fund our growth. We thought there might be a possibility if we continued to make these hits and churn them out at a pace, a certain pace, that we could actually use the cash flows to fund our growth, like the way normal businesses do. And That is actually a very exciti…

AI assessment note: “we thought we could have a way to self-fund our growth... that was kind of our dilemma.”

Q totally different company, and I'm quoting here, I'm quoting Alex, uh, and by different I mean worse. So how do you as the co-founder try and maintain this kind of sense of small company culture with deep links internally as you do grow excessively? I think you mentioned that you were going to be 65 or 70 staff. In two years time. How do you keep that small company culture?

A Yeah, we do it. So we do a few things to, um, to, uh, Gimla does have a culture. Um, I think it's a fairly strong culture, although we haven't been that explicitly about communicating it and what it is, and I think that's something we'll probably start to do. And the ways we, uh, I mean, I think the way culture gets communicated is the behavior of the leadership. And also you can design in certain kind of signs and language and vocabulary that people use. So we started something recently called Gimlet Guides, which is every new employee who starts at the company now. It's something we started just a few months ago. We didn't have at the beginning, but when we got to like 20 or 25 people, we decided to get formalized about the onboarding process into the company. And so now when you come into the company, you're introduced to someone who's called your Gimlet Guide. And Gimlet Guides are people who are selected because they Are, um, they get our culture, and they're very empathetic, and they have meant, like, they have it in them to be a mentor, and so it's sort of their job to also, like, establish and communicate what the culture is here, um, how we work, um, what we believe in, what we don't believe in.

AI assessment note: “we started something recently called Gimlet Guides”

Q And moving back to the raise, I'd love to discuss Tim and Graham Holdings now, uh, your lead investor, and we had a little on the show, uh, about the raise, but were there any hiccups, and were you tempted by any other offers, maybe the value Gimlet higher? What, what was the situation there?

A When we set out to, to raise the Series A, we sort of explicitly told each other that, um, the terms were not the most important thing to us, so we weren't, we weren't out trying to drive the highest valuation. Um, what was more important to us is that we had a, that we could have a partner that, like, really understood us, and that was aligned on the vision, and had experience investing in media, because I think investing in media is different than investing in technology companies, and the returns have a different, uh, Timeline. And the way the dynamics of media companies are just different than tech companies. So, um, those were the things that were important more than the valuation, I guess, or the other stuff. Um, I mean, it was really important to Alex and I that we both still controlled our own destiny, that we controlled more than 50% of the company, and we wanted to have a small board. And then when we, um, the round went very well, and there, there, there was a lot of interest in our company because podcasting is kind of a hot space, but there aren't A lot of investable companies in this space.

AI assessment note: “we sort of explicitly told each other that, um, the terms were not the most important”

Q And moving back to the raise, I'd love to discuss Tim and Graham Holdings now, uh, your lead investor, and we had a little on the show, uh, about the raise, but were there any hiccups, and were you tempted by any other offers, maybe the value Gimlet higher? What, what was the situation there?

A When we set out to, to raise the Series A, we sort of explicitly told each other that, um, the terms were not the most important thing to us, so we weren't, we weren't out trying to drive the highest valuation. Um, what was more important to us is that we had a, that we could have a partner that, like, really understood us, and that was aligned on the vision, and had experience investing in media, because I think investing in media is different than investing in technology companies, and the returns have a different, uh, Timeline. And the way the dynamics of media companies are just different than tech companies. So, um, those were the things that were important more than the valuation, I guess, or the other stuff. Um, I mean, it was really important to Alex and I that we both still controlled our own destiny, that we controlled more than 50% of the company, and we wanted to have a small board. And then when we, um, the round went very well, and there, there, there was a lot of interest in our company because podcasting is kind of a hot space, but there aren't A lot of investable companies in this space.

AI assessment note: “we weren't out trying to drive the highest valuation.”